1,3-Dibromo-5,5-dimethylhydantoin → 4-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol

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Reaction Conditions

Reaction Steps

To a cooled (−20° C.) solution of 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol (1.20 g, 5.82 mmol) in tetrahydrofuran (30 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (832 mg, 2.91 mmol) in 4 portions over 10 min. The mixture was allowed to stir (−20° C.) for 3 h. The reaction was quenched with the addition saturated aqueous Na2SO3 (30 mL) and was allowed to warm to rt. The mixture was extracted with ethyl acetate (3×25 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The crude material was purified by ISCO® chromatography using a gradient of 75% to 100% ethyl acetate in hexanes to afford 1.2 g (72%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.81 (s, 1 H), 6.60 (s, 1 H), 4.37 (t, 1H), 3.39 (q, 2 H), 2.80 (t, 2 H), 1.70-1.60 (m, 2 H), 1.48-1.39 (m, 2 H); ES-MS m/z 285.1 [M+H]+, HPLC RT (min) 1.55.

Provenance & Evidence